(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran

Base Information

Chemical Name:(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran
CAS No.:264197-95-7
Molecular Formula:C₂₂H₃₄N₂O₆
Molecular Weight:422.522
Hs Code.:

Synonyms:(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran

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Chemical Property of (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran

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Technology Process of (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran

There total 5 articles about (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: ((4S,5R)-4-Benzyloxycarbonylamino-5-hydroxy-7-oxiranyl-heptyl)-carbamic acid tert-butyl ester

: 264197-95-7
(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 7733-29-1,199924-46-4
Z-Orn(Boc)-OH

: 264197-95-7
(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,N'-diisopropyl carbodiimide / CH₂Cl₂ / 4 h / 20 °C

2.1: Mg / diethyl ether / 1 h / Heating

2.2: LiCl; CuCN / tetrahydrofuran / 0.25 h / -40 °C

2.3: 3.72 g / tetrahydrofuran / 0.67 h / -78 - -5 °C

3.1: 46 percent / L-Selectride / tetrahydrofuran / 1 h / -100 - -70 °C

4.1: MCPBA / CH₂Cl₂ / 3.5 h / 20 °C

5.1: 670 mg / PPTS / CH₂Cl₂ / 12 h / 20 °C

With pyridinium p-toluenesulfonate; L-Selectride; magnesium; 3-chloro-benzenecarboperoxoic acid; diisopropyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Esterification / 2.1: Metallation / 2.2: Substitution / 2.3: Acylation / 3.1: Reduction / 4.1: Epoxidation / 5.1: Ring cleavage;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 294664-65-6
2-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentanethioic acid S-pyridin-2-yl ester

: 264197-95-7
(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)-2-hydroxymethylentetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: Mg / diethyl ether / 1 h / Heating

1.2: LiCl; CuCN / tetrahydrofuran / 0.25 h / -40 °C

1.3: 3.72 g / tetrahydrofuran / 0.67 h / -78 - -5 °C

2.1: 46 percent / L-Selectride / tetrahydrofuran / 1 h / -100 - -70 °C

3.1: MCPBA / CH₂Cl₂ / 3.5 h / 20 °C

4.1: 670 mg / PPTS / CH₂Cl₂ / 12 h / 20 °C

With pyridinium p-toluenesulfonate; L-Selectride; magnesium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Metallation / 1.2: Substitution / 1.3: Acylation / 2.1: Reduction / 3.1: Epoxidation / 4.1: Ring cleavage;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z